Bioinspired Collective Syntheses of Iboga-Type Indole Alkaloids.
Gaoyuan Zhao, Xingang Xie, Haiyu Sun, Ziyun Yuan, Zhuliang Zhong, Shouchu Tang, Xuegong She
Organic Letters May 20, 2016 DOI: 10.1021/acs.orglett.6b00989 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Ibogaine |
| Keywords | Bioinspired synthesis Biomimetic synthesis Collective synthesis Chemical synthesis Organic synthesis Natural product synthesis Complex molecule synthesis Iboga alkaloid synthesis Indole alkaloids Iboga alkaloids Ibogamine Natural compounds Complex natural products |
| Citations | 64 |
| Key points | Proposes that a bioinspired collective synthesis strategy can produce seven iboga-type indole alkaloids, with tabertinggine serving as a precursor for further biomimetic transformations. |
Abstract
We present the application of a bioinspired collective synthesis strategy in the total syntheses of seven iboga-type indole alkaloids: (±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D. In particular, tabertinggine and its congeners serve as iboga precursors for the subsequent biomimetic transformations into other iboga-type alkaloids.
Comparable studies
Other theoretical and historical papers on ibogaine, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Biosynthesis of an Anti-Addiction Agent from the Iboga Plant. | 2019 | Theoretical or philosophical paper | |
| Fatalities after taking ibogaine in addiction treatment could be related to sudden cardiac death caused by autonomic dysfunction. Humans | 2006 | Theoretical or philosophical paper | |
| Iboga Alkaloids. II.1 the Structures of Ibogaine, Ibogamine and Tabernanthine | 1957 | Theoretical or philosophical paper | |
| Ibogaine analogues. Synthesis and preliminary pharmacological evaluation of 7-heteroaryl-2-azabicyclo[2.2.2]oct-7-enes. | 2003 | Theoretical or philosophical paper | |
| Understanding the Healing Potential of Ibogaine through a Comparative and Interpretive Phenomenology of the Visionary Experience | 2018 | Theoretical or philosophical paper |
Citations in the library
Cited by 4
- Efficient and modular synthesis of ibogaine and related alkaloids. Nature Chemistry March 1, 2025
- Reactivity of the Iboga Skeleton: Oxidation Study of Ibogaine and Voacangine. Journal of Natural Products June 23, 2023
- Disrupting Substance Use Disorder: The Chemistry of Iboga Alkaloids. European journal of organic chemistry September 23, 2024
- The iboga enigma: the chemistry and neuropharmacology of iboga alkaloids and related analogs. Natural Product Reports March 4, 2021
Cites 4
- The Olivocerebellar Projection Mediates Ibogaine-Induced Degeneration of Purkinje Cells: A Model of Indirect, Trans-Synaptic Excitotoxicity Journal of Neuroscience November 15, 1997
- The Alkaloids of Tabernanthe iboga. Part IV.1 The Structures of Ibogamine, Ibogaine, Tabernanthine and Voacangine Journal of the American Chemical Society 1958
- Ibogaine reduces organ colonization in murine systemic and gastrointestinal Candida albicans infections. Journal of medical microbiology July 1, 2005
- Iboga-Type Alkaloids from Ervatamia officinalis. Journal of Natural Products August 22, 2014